Water → (3 S)-1-[5-Chloro-3-[(4-methoxyphenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol

HRID 2179101Notes

Reaction equation

HRID 2179101 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.CC[N:23]([CH:27]([CH3:29])C)[CH:24]([CH3:26])C.[OH2:30]>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([N:23]2[CH2:24][CH2:26][C@H:29]([OH:30])[CH2:27]2)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 81531DiisopropylethylamineHCID 582908695,7-dichloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Product 1

HCID 89587064(3 S)-1-[5-Chloro-3-[(4-methoxyphenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5,7-Dichloro-3-(4-methoxy-benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 109, b) (2.95 g), (S)-pyrrolidinol (1.82 g, 20.9 mmol) and DIPEA (9.83 g, 76.1 mmol) in DCM was stirred at room temperature for 30 min. The mixture was poured into water, extracted with DCM and the combined organic layers were dried with MgSO4, filtered and evaporated to yield the crude title compound which was used in the consecutive step without further purification. MS (m/e): 361.3 (MH+).

Workup

  1. extractionextracted with DCM
  2. dry with materialthe combined organic layers were dried with MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-dfdd09f019c44b8bb346d2fcc95d22a0
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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